Process for the manufacture of monovalent phenols from mono-chloro-substitution products of aromatic hydrocarbons.



UNITED STATES PATENT OFFICE.

KURT H. MEYER, MUNICH AND FRIEDRICH BERGIUS, F HANOVER, GERMANY.

PRCCE$S FOR THE .MANUFACTURE OF MONOVALENT PHENOLS FROM MONO-CHLORO- SUBSTITU'IION PRODUCTS ,0]? AROMATIC HYDROCARBONS.

No. Drawing.

Specification of Letters Patent. Patented May 20, 1913. Application filed November 11, 1912. Serial No. 730,788.

To all whom it may-concern:

Be it known that We, KURT H. MEYER, chemist, and FRIEDRICH BERGIUS, chemist, citizens of the German Empire, residing at (1 Munich and (2)v Hanover, in Germany,

have invented certain new and useful Improvements in the Process for the Mannfacture ofMonovalent Phenols from Mono- Chloro-Substitution Products of Aromatic specification.

In order to manufacture phenols from aromatic hydrocarbons it is necessary to sul- Jfonate the latter and to fuse the sulfo-acids with potash or soda. As starting material for phenol, however, beside the benzenesulfo-acid also chloro-benzene may be used. Until now, only the chloro compounds 'of aromatic hydrocarbons which contain, beside chlorin, another substituent, for instance a nitro group in the nucleus, could-be transformed into the corresponding hydroxyl compound by treatment with diluted sodium hydroxid; but it was impossible to transform aromatic chlorin compounds in which the aflinity of the chlorin atom is not weakened by a second negative substituent, into hydroxyl compounds by heating them with water or caustic alkali (NaOI-I) up to the boiling point.' Now'it has been found that these reactions, impossible under ordinary conditions, readily occur if the halogen hours under pressure at 300 C. By salting out, 5 partsof phenol can be obtained from the aqueous solution. The greater part of the chloro-benzene has remained unchanged and can be submitted anew to the same treatment.

Example II: 100 parts of 'chloro-benzene are heated with 400 parts of soda solution of 10 per cent. strength in a closed vessel for eight hours to 280300 O. The. yield in phenol which separates out in an almost colorless condition after acidiilation with concentrated sulfuric acid, amounts to 70 parts byweight per 100 parts by weight of the chloro-benzene used. Small quantities (about 10 per cent.) of an oil having a boiling point of 240 C. are also formed.

Example III: 100 parts of oz-chloro-naphthalene is mixed with 300 partsof soda solution of 10 per cent. strength, and the mixture is heated during 6. hours under pressure to 280300 C. Almost the whole of.

the a-c'hloro-naphthalene is thereby dissolved, showing a slight brownish color, while a small quantity remains behind in the form of a brown smeary mass. On acidulating the alkaline solution and crystallizing out, a yield of 50-60 percent. of perfectly pure oc-naphthol is obtained.

Having now described our invention what we claim as new and desire to secure by Letters Patent is I 1. The process of manufacturing monovalent phenols from mono-chloro-substitution' products of aromatic hydrocarbons, which consists in heating the mono-chlorosubstitution products with Water to a high temperature under pressure.

2. The process for the manufacture of mono-valent phenols from mono-chloro-substitution products of aromatic hydrocarbons, which consists in heating'said substitution products under pressure at a high temperature with water containing caustic alkali for neutralizing the hydrochloric acid that may be formed.

3. The process for the manufacture of mono-valent phenols from mono-halogensubstitution products of aromatic hydrocarbons, which consists in heating said substitution products under pressure at a high temperature with water.

In testimony whereof, We afiix our signatures in presence of two witnesses. KURT H. MEYER.

, FRIEDRICH BERGIUS.

Witnesses as to signature, of Kurt 'H. Meyer: a

' A. V. W. CorrER,

MATHI'LDE K. HELD.

Witnesses as to signature of Friedrich Bergius:

ROBERT H. HINoKLnY, ARTHURJ. BUNDY. 

